Benzyl Chloride → Benzyl ethanimidothioate--hydrogen chloride (1/1)

HRID 1420133Notes

Reaction equation

HRID 1420133 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[CH2:5]([Cl:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[ClH:12].[CH2:5]([S:3][C:1](=[NH:4])[CH3:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 2723949Thioacetamide2×

Product 1

HCID 12626231Benzyl ethanimidothioate--hydrogen chloride (1/1)Yield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of thioacetamide (15.0 g, 0.20 mol) and benzyl chloride (25.3 g, 0.20 mol) in chloroform (75 ml) was heated under reflux for 90 minutes (the thioacetamide required ~40 minutes to go into solution). The reaction mixture was then allowed to cool to room temperature and was then stood at 0° C. overnight, when colourless crystals formed as a layer on the surface. The product was filtered off, washed with cold 10% ether-chloroform and sucked dry to give the title compound (25.55 g) as colourless prisms. Mpt.=161°-163° C.

Workup

  1. temperaturewas heated
  2. customwhen colourless crystals formed as a layer on the surface
  3. filtrationThe product was filtered off
  4. washwashed with cold 10% ether-chloroform
  5. customsucked dry

Sources & evidence

ORD record
ord-e3f3cf00d8d04a71afa7124bed4f755d
Source dataset
uspto-grants-1999_03
Patent number
US05889056

Reaction notes

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